7-bromo-1H,2H,3H,5H-pyrido(2,3-e)(1,4)oxazepin-2-one → 7-bromo-1H,2H,3H,5H-pyrido[2,3-e][1,4]oxazepine

Temperature

0 °C

To a solution of 3-Bromo-5,9-dihydro-6-oxa-1,9-diazabenzocyclohepten-8-one (1.0 g, 4.13 mmol) in THF (40 mL) at 0° C. was added BH3 (30 mL of a 1.0 M solution in THF, 30.0 mmol). The solution was heated to reflux. After 18 h, the solution was cooled to 0° C. and the reaction quenched with H2O (2.5 mL). The mixture was concentrated and the resulting off-white solid was dissolved in MeOH (30 mL) and NaOH (15 mL of a 2 N solution). The mixture was heated at reflux for 4 h. The MeOH was removed under reduced pressure. The resulting precipitate was collected by filtration and washed with H2O (20 mL). The wJiite solid was dried to give the title compound (0.360 g, 38%). 1H NMR (300 MHz, DMSO-d6) δ8.06 (d, J=23 Hz, 1H), 7.71 (d, J=2.3 Hz, 1H), 6.55 (br s, 1H), 4.47 (s, 2H), 3.74-3.70 (m, 2H), 3.16-3.12 (m, 2H); ESI MS m/z 229 (100%); 231 (100%) [C8H9BrN2O+H]+.

1. temperatureThe solution was heated to reflux
2. customthe reaction quenched with H2O (2.5 mL)
3. concentrationThe mixture was concentrated
4. dissolutionthe resulting off-white solid was dissolved in MeOH (30 mL)
5. temperatureThe mixture was heated
6. temperatureat reflux for 4 h
7. customThe MeOH was removed under reduced pressure
8. filtrationThe resulting precipitate was collected by filtration
9. washwashed with H2O (20 mL)
10. customThe wJiite solid was dried

ORD record

ord-d55c9b12ca6044b98eabaae37465661f

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895545B2